Watch Your Heads
by sinful delight
Summary: The Winchester boys are called to duty when the Headless Horseman rides again.
1. Prologue

**Watch Your Heads**

Summary: The Winchester boys are called to duty when the Headless Horseman rides again.  
Rated: T  
Disclaimer: Sadly the Winchester's aren't mine. I do own Mark however.  
Author's Note: This idea's been floating around in my head for a while now. (no pun intended) After much thought and deliberation I decided that I just _had_ to write it down. I hope you enjoy it, please review! You have no idea what it does for my confidence if I know people want me to continue.

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**Prologue **

Mark wandered down Main Street with his faithful dog Pepper at his side. It was late and Mark was tired from a long day of working at the discount market on the outskirts of town. He had been more than eager to head to bed but Pepper had suggested otherwise. Mark really couldn't be angry with the dog. When duty call… well you know the saying.

So here he was, well after midnight, walking his dog down Main Street in his bathrobe. Not that there was anyone around to see him in his bathrobe, mind you. The street was completely deserted.  
Pepper stopped to sniff a particularly interesting bush. Mark waited patiently, hoping that Pepper would do his business soon so that he could return to his nice warm apartment.

The sound of hooves clattering on the road startled Mark out of his thoughts. He peered towards the sound, trying to catch a glimpse what could be causing the noise. In the distance, he could just make out the outline of a horse galloping down the middle of the rode.

Mark rubbed his eyes. Surely he must be dreaming. Who on earth would be riding a horse down Main Street in this day and age? And at this hour?

He turned toward Pepper to his if his trusty dog had yet to notice the horse but Pepper had disappeared. Mark cursed. So much for his loyal and faithful friend.

The horse was approaching at an alarming rate. Mark squinted at the figure as it drew nearer. Something wasn't right here, if only he could figure out what. As the horse drew closer, Mark suddenly realized what it was.

The person riding the horse was headless!

Mark's eyes grew wide in terror. He turned and began running down the road as fast as he could. His slippers made a flip flopping noise as he tried to race to safety.

The horse was nearing, he could hear the hooves beating on the pavement. He willed himself not to look back, to just keep going.

This is why Mark did not see the blow coming as the horseman raised his sword and with one fluid motion, swung.

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	2. Chapter 1: The Legend

**Watch Your Heads**

Summary: The Winchester boys are called to duty when the Headless Horseman rides again.  
Rated: T  
Disclaimer: I woke up Christmas morning to find no Dean or Sam under my tree with a bow. frowns Oh well, maybe next year…  
Author's Note: It's taken me a while to update and for that I apologize. I wanted to read the Legend of Sleepy Hollow fully though so I could actually make it so Sam sounds like he knows what he's talking about in this chapter. I'm trying my best to stick with the actual legend and not the movie.  
The next update will be sooner, I promise!

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Chapter 1: The Legend

It was a good morning for Dean. He had gone out to get breakfast at the local diner, a quaint little place. The food had been good, not to mention that the waitress's shirt had been about four sizes too small, giving Dean something to smirk about the entire way back to the motel.

Dean threw the door to the motel room open, flooding the small space with light.

"Morning Sammy!" Dean shouted, as he kicked the door closed behind him.

Sam was sitting at the small table in the corner with the laptop. He glanced over at Dean, catching the glimpse of his smirk.

"The waitress was barely clothed again wasn't she?" Sam asked with a sigh.

Dean didn't answer but his smile grew wider.

"Here, I brought you a breakfast sandwich to start the day off right!" Dean threw Sam a bag that was stained with grease. He grabbed the other chair situated at the table and plopped down in it while Sam dug the sandwich out of the bag.

"So, did you find us another hunt on that thing or am I going to have to do everything myself?" Dean replied, glancing at the laptops screen.

Sam downed the sandwich, wiping the crumbs off of his mouth with his sleeve. Turning back to the computer he read. "The police found the body of thirty-one year old Edward Little Tuesday morning. Little's head had been decapitated from his body, the third to be discovered as such. Investigator's are looking into the three murders. They currently have no suspects."

Dean frowned. "I don't know, Sammy. It doesn't sound like our kind of thing. Just because some psycho is out there, chopping off people's heads doesn't mean that it's supernatural."

Sam nodded. "True, except that this took place in Sleepy Hollow. It's at least worth checking out."

Dean sighed, leaning back in the chair. He remained silent for a moment, mulling over the options.

"Alright, let's go."

Half an hour later the boys were packed into the Impala with their meager belongings, headed toward Sleepy Hollow, New York. Sam sat in the passenger seat, looking up information with Dean's music blasting in his ear.

Sam reached over toward the radio only to have Dean slap his hand away.

"Don't touch it Sammy!" Dean growled.

"I just want to turn it down so I can hear myself think!" Sam shouted to be heard over the blaring of Metallica.

Dean turned the music down, leaving Sam with a slight ringing in his ears. "That better?"

"It's a start." Sam returned to looking up research. After a few minutes of silence, Dean could not bear to keep quiet any longer.

"So… Find anything?"

Sam nodded. "Listen to this. 'The Legend of Sleepy Hollow' was written in 1819 under the pen name of 'Geoffrey Crayon, Gent', other wise known as Washington Irving. Sleepy Hollow is said to be filled with ghostly apparitions and supernatural occurrences. The most famous of these is none other than The Headless Horseman, also known as the Galloping Hessian of the Hollow. The Horseman is said to be a solider from the Revolutionary War, whose head was blown off by a cannonball. He rides upon a black horse, haunting the area near the Old Dutch Church where he is said to be buried in an unmarked grave."

"So he chops off people's heads, searching for his own?" Dean interrupted.

"So the legend goes," Sam said with a shrug. "In all actuality however, the story goes on to say it is just that, a story, told around the fire for means of entertainment, often times as a prank to scare off outsiders."

"You and I know well enough that most stories have at least some truth to them," Dean pointed out.

Sam remained silent for a second, lost in thought.

"Sometimes I wish I didn't," he said quietly.

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End file.
